This invention relates to oxobicyclononane derivatives defined according to the structure: ##STR12## wherein X, Y, X' and Y' each represents the moiety having one of the structures: ##STR13## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond with the proviso that when X' and Y' are each the moiety: ##STR14## then the dashed line at the "2-3" position is a carbon-carbon double bond and the dashed line at the "6-7" position is a carbon-carbon single bond and one of X or Y has the structure: ##STR15## and the other of X or Y has the structure: ##STR16## and with the further proviso that when X and Y are the moieties: ##STR17## then the dashed line at the "6-7" position is a carbon-carbon double bond and the dashed line at the "2-3" position is a carbon-carbon single bond and one of X' or Y' has the structure: ##STR18## and the other of X' or Y' has the structure: ##STR19## and wherein R represents hydrogen, C.sub.1 -C.sub.3 acyl or C.sub.1 -C.sub.2 alkoxy carbonyl with the major portion of the mixtures defined according to the generic structure: ##STR20## wherein one of X or Y is the moiety: ##STR21## with R being defined as being hydrogen, C.sub.1 -C.sub.3 acyl or C.sub.1 -C.sub.2 alkoxy carbonyl.
Included in the foregoing genus having the structure: ##STR22## is the genus of compounds having the structure: ##STR23## wherein R represents methyl or ethyl; one of the dashed lines represents a carbon-carbon single bond or a carbon-carbon double bond; N and P each represents 0 or 1; the sum of N and P being equal to 1; with the proviso that when N is 1, the dashed line at the "2-3" position is a carbon-carbon single bond and the dashed line at the "6-7" position is a carbon-carbon double bond and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles.
Also covered by this invention are the precursor formates defined according to the structure: ##STR24## wherein the dashed lines, N and P are defined, supra.
Materials which can provide strawberry, rosy, banana, woody, piney, minty, fruity and jasmine aromas with floral, fruity, spicy, green, hawthorne, ozoney and anisic topnotes are highly desirable in the art of perfumery. Many of the natural substances which provide such fragrance nuances and contribute the desired nuances to perfumery compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
The prior art contains a large number of teachings regarding the use of organic carbonates in augmenting or enhancing the aroma of perfumes. Thus, U.S. Pat. No. 4,033,993 discloses the use of organic carbonates defined according to the structure: ##STR25## wherein R.sub.1 is a moiety having from 8 to 12 carbon atoms selected from the group consisting of alkylcyclohexyl, alkenylcyclohexyl, alkynylcyclohexyl and cycloalkyl and R.sub.2 is a moiety selected from the group consisting of alkyl having from 1 to 5 carbon atoms, alkenyl having from 2 to 5 carbon atoms and alkynyl having from 2 to 5 carbon atoms. U.S. Pat. No. 4,033,993 describes, for example, methyl-1-ethynycyclohexyl carbonate having a fruity, herbal complex odor and distinct fragrance of dill. In addition, U.S. Pat. No. 4,033,993 describes methyl cyclooctyl carbonate as having a herbal, natural and complex fragrance which is distinguished by a strong and long clinging flowery jasmine scent and further indicates its use in jasmine perfume compositions. U.S. Pat. No. 4,033,993 describes the preparation of the compounds defined according to the structure: ##STR26## according to the reaction: ##STR27## wherein R.sub.1 and R.sub.2 are defined as above.
In addition, U.S. Pat. No. 4,080,309 described the perfume use of the carbonates defined according to the structure: ##STR28## wherein R.sub.1 ' is a moiety having from 8 to 12 carbon atoms selected from the group consisting of alkylcyclohexyl, alkenylcyclohexyl, alkynylcyclohexyl and cycloalkyl and R.sub.2 ' is a moiety selected from the group consisting of alkyl having from 1 to 5 carbon atoms, alkenyl having from 2 to 5 carbon atoms and alkynyl having from 2 to 5 carbon atoms. Described in U.S. Pat. No. 4,080,309 are also such compounds as methyl cyclooctyl carbonate and the use thereof in jasmine perfume formulations. As is the case in U.S. Pat. No. 4,033,993, the carbonates of U.S. Pat. No. 4,080,309 are indicated to be prepared according to the reaction: ##STR29##
4-Cyclooctenyl alkyl carbonates defined according to the structure: ##STR30## wherein R.sub.4 is methyl or ethyl and reaction products including a major proportion of said 4-cyclooctenyl alkyl carbonates and a minor proportion of bicyclooctanyl carbonates having the structure: ##STR31## wherein R.sub.5 is methyl or ethyl and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles are described in U.S. Pat. No. 4,452,730 issued on June 5, 1984.
Tricyclodecane carbonates having the structures: ##STR32## are described as having fruity (apple), anisic-like aromas with dry, hay-like and berry-like undertones.
However, nothing in the prior art describes the oxobicyclononane derivatives of our invention or the organoleptic utilities thereof.